Lithium Hydroxide → (S)-5-((S)-4-carboxy-1-(4-iodobenzylamino)-1-oxobutan-2-ylamino)-5-oxo-4-(3-(4-sulfamoylphenyl)thioureido)pentanoic Acid

HRID 333134Notes

Reaction equation

HRID 333134 reaction equation
[I:1][C:2]1[CH:42]=[CH:41][C:5]([CH2:6][NH:7][C:8](=[O:40])[C@@H:9]([NH:16][C:17](=[O:39])[C@@H:18]([NH:25][C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([S:35](=[O:38])(=[O:37])[NH2:36])=[CH:31][CH:30]=2)=[S:27])[CH2:19][CH2:20][C:21]([O:23]C)=[O:22])[CH2:10][CH2:11][C:12]([O:14]C)=[O:13])=[CH:4][CH:3]=1.[OH-].[Li+]>CO.O>[C:12]([CH2:11][CH2:10][C@H:9]([NH:16][C:17](=[O:39])[C@@H:18]([NH:25][C:26]([NH:28][C:29]1[CH:30]=[CH:31][C:32]([S:35](=[O:37])(=[O:38])[NH2:36])=[CH:33][CH:34]=1)=[S:27])[CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:8]([NH:7][CH2:6][C:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:42][CH:41]=1)=[O:40])([OH:14])=[O:13]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86632285(S)-methyl 5-(4-iodobenzylamino)-4-((S)-5-methoxy-5-oxo-2-(3-(4-sulfamoylphenyl)thioureido)pentanamido)-5-oxopentanoate

Product 1

HCID 86632286(S)-5-((S)-4-carboxy-1-(4-iodobenzylamino)-1-oxobutan-2-ylamino)-5-oxo-4-(3-(4-sulfamoylphenyl)thioureido)pentanoic AcidYield 25.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of (S)-methyl 5-(4-iodobenzylamino)-4-((S)-5-methoxy-5-oxo-2-(3-(4-sulfamoylphenyl)thioureido)pentanamido)-5-oxopentanoate (0.200 g, 0.27 mmol) and lithium hydroxide (48 mg) in methanol (3.0 mL) and water (1.0 mL) was stirred at room temperature for overnight. The reaction mixture was purified by HPLC to give the title product (49.4 mg) as a yellow solid. MS (ESI), 728 (M+Na)+.

Workup

  1. customThe reaction mixture was purified by HPLC

Sources & evidence

ORD record
ord-32e53b8a481d474b9074c2cce1521d5c
Source dataset
uspto-grants-2014_11
Patent number
US08877970B2

Reaction notes

Loading…